14966-69-9

Usage

InChI:InChI=1/C8H14O4/c1-4-12-8(10)6(2)7(9)5-11-3/h6H,4-5H2,1-3H3

Upstream product

• 1738-36-9 2-methoxyacetonitrile 
• 535-11-5 Ethyl 2-bromopropionate 
• 6290-49-9 methyl methoxyacetate 
• 38870-89-2 Methoxyacetyl chloride 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 

Downstream Products

• 67187-95-5 (E)-3-(4-Acetylamino-2,5-dimethoxy-phenylamino)-4-methoxy-2-methyl-but-2-enoic acid ethyl ester 
• 83094-55-7 3-[(2,4-Dinitro-phenyl)-hydrazono]-4-methoxy-2-methyl-butyric acid methyl ester 

Relevant academic research and scientific papers

Pyrimidine derivatives and processes for the preparation thereof

The present invention relates to novel pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts thereof which possess an excellent anti-secretory activity, pharmaceutical compositions containing the same as an active ingredient, their novel intermediates, and processes for the preparation thereof wherein: when A is piperidin-1-yl or —NH—B, wherein B is C3-C4alkyl, C3-C4alkenyl, C3-C7cycloalkyl, C1-C3alkoxyethyl, phenylethl which may be substituted or unsubstituted, 3-trifluoromethylphenylmethyl, 1-naphthylmethyl, 4-methylthiazol-2-yl or 4-phenylthiazol-2-yl, R1is hydrogen or methyl; and R2, R3, R4and R5are hydrogen; or when A is a group of formula (II); when R1is hydroxymethyl or C1-C3alkoxymethyl, R2, R3, R4, R5and R6are hydrogen; and R7is hydrogen or halogen; or when R1is hydrogen or methyl, R7is hydrogen or halogen; and one or two of R2, R3, R4, R5and R6is hydroxy, methoxy, or a group of formula (III) wherein Z is C1-C4alkyl, substituted or unsubstituted C1-C4alkenyl, cyloalkyl, benzyloxyalkyl, alkoxycarbonylalkyl, morpholinomethyl, piperidinomethyl, 4-substituted-piperazinomethyl, substituted or unsubstituted phenyl, naphthyl, substituted or unsubstituted benzyl, thiophen-2-yl-methyl, 1-substituted-pyrrolidin-2-yl or —CHR8NHR9, wherein R8is hydrogen, methyl, isopropyl, benzyl, benzyloxymethyl, methylthioethyl, benzyloxycarbonylmethyl, carbamolymethyl, carbamoylethyl, or 1-benzylimidazol-4-ylmethyl and R9is hydrogen or t-butoxycarbonyl; and the others are hydrogen or methyl.

FAILURE TO VERIFY A REPORTED SYNTHESIS OF THE ACONITINE SKELETON

Attempts to verify the first three stages of a claimed synthesis of the aconitine skeleton (Samir Chatterjee, Tetrahedron Lett. 3249 (1979) have given totally different results.It is concluded that the reported products of these three stages were not in fact obtained.